


It Feels Like This

by Anonymous



Series: Adventures in Jack's sexual awakening [2]
Category: Supernatural
Genre: Dirty Talk, Hand Jobs, M/M, Masturbation, Oral Sex, Plot What Plot/Porn Without Plot, Porn Watching
Language: English
Status: Completed
Published: 2020-03-08
Updated: 2020-03-08
Packaged: 2021-03-01 00:27:43
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,733
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23066230
Author URL: https://archiveofourown.org/
Summary: When Sam and Dean leave for a case, Jack takes advantage of the time alone in the bunker to pleasure himself to a hot video he finds on Dean's laptop.
Relationships: Implied Jack Kline/Dean Winchester
Series: Adventures in Jack's sexual awakening [2]
Series URL: https://archiveofourown.org/series/1657693
Comments: 6
Kudos: 79
Collections: Supernatural Anon Kink Meme





	It Feels Like This

**Author's Note:**

> Based on [this](https://spnkink-meme.livejournal.com/157542.html?thread=47502438#t47502438) prompt.

Jack was still buzzing from what happened the night a couple of days ago. New doors had opened for him that night, and then they had shut just as quickly. He'd gotten nothing more than a peak, and then things had gone back to normal. Dean and Sam had been crouched over with books and newspaper clippings on the living room table for four days, mapping out clues and evidence as they worked on a case involving what they assumed were ghouls gone rogue. Castiel was, well, Jack wasn't sure. Castiel wasn't always the most talkative or entrusting person when it came to plans or information. Jack supposed he would find out where Castiel was once he came back to tell them all about his recent ventures.

Though, despite the Winchesters being knee-deep in investigating the ghouls, and Castiel being absent, Jack didn't feel like he had enough time alone to continue exploring the world of sex. He wanted more, wanted to experiment and experience completion by his own hands, figure it out by himself, but to do so he needed to be alone.

It took another two nights, and then it finally happened.

"Hey, Jack," Sam said, opening his door at the same time as he knocked, clearly lacking a sense of privacy.

Still, Jack smiled softly to greet him. "Sam."

"Uh, so, Dean and I are heading out. Won't take more than a couple of days. You'll, uh, you'll be alright here by yourself?"

Sam adjusted the duffel on his shoulder.

"Yes. I will be okay."

"And if not you'll-"

"I'll call you." Jack said, finishing Sam's sentence which earned him a small smile.

"Yeah, good. Just wanted to double check."

"I will be fine."

"SAMMY," Dean's voice echoed from somewhere down the hall. "We gotta roll. The ghouls ain't gonna kill themselves."

Sam rolled his eyes and let out a grunt. "Yeah okay. Call us if anything comes up."

  
Then, finally, they were out of there.

~ ~ ~

The last time Jack tried this, he hadn't really known how to. Getting excited and turned on wasn't the problem, especially not after what happened last week. It didn't take more than a few thoughts of Dean's strong hand wrapped around the length of him to make him half hard. _The problem_ was dealing with it. Getting off. Knowing how to, without getting caught up in a feeling of confusion, or a strange sense of shame about what he was doing.

It was complicated, really. Jack couldn't figure out how humans made it look so easy in porn. How someone would let another man or woman 'go to town' on them like that, like Dean would say.

Wow. He tilted his head to the side and watched the screen intensely as a man plowed his hard manhood deep into a woman who was bent over a couch. Her moans echoed against the stone walls, and she let out tiny shrieks and yelps every time the man slammed back into her.

To be completely honest, the porn didn't do much to Jack in terms of horniness. If anything, he watched it more for an educational purpose, fascinated by the different positions and the general technicalities of the different videos. The way the woman's tits bounced up and down with every thrust of the man's hips; the way he grabbed them seconds later and squeezed one of them like a… a stress ball. It looked far from comfortable.

It was when Jack realized that he was more aware of the deep crease that had made itself a home between his eyebrows, rather then the task at hand of getting his dick back to where it had been before the video, that he decided to switch clips and look for something different. Going only by the recommended videos that had popped up when he had opened the website on Dean's laptop maybe wasn't the best idea. There had to be something more, something different.

Jack browsed the website for a minute, his eyes wandering over the tiny squares that displayed different close-ups of women in various exposing positions. Neither the thumbnails nor the titles left much to the imagination.

He sighed.

This wasn't what he wanted to see, he realized, left hand slack over his clothed dick. He closed his eyes and allowed himself a moment to go back in time and relive that fidgety, exciting time when the door to this whole new world of arousal and completion had been opened for him for the first time.

Once his head was back in the game, Jack raked his eyes over the porn site again, set on finding something else. He wasn't sure what, yet, but he was determined to find _something_.

In the top right corner of the screen sat a small icon shaped as something that looked kind of like a person, or a mannequin, and it was glowing green. He hovered the cursor over it and, Jack sat back and his mouth fell open a little in surprise when a whole sidebar appeared, unfurling down from the icon to reveal various titles and sections.

" _Zepp_69_ …" he read quietly, eyes trailing over the letters and the different options and categories that had showed up in the sidebar. Then it hit him.

Dean was logged in.

_Of course_. It was his laptop, after all.

Curious, Jack traced the cursor over the sidebar and the titles displayed there. _Settings, Profile, Inbox(2), Favorites, Log out_ … Wait, that was it. _Favorites_.

Going by the video clips he had been greeted by on the front page of the website, Jack expected to be met by similar content when he dared to click the mouse over the title. Naked women, close ups of their genitals, large breasts and faces with open mouths and half-lidded eyes covered in white goo.

He couldn't have been more wrong.

"Oh."

Like Dean would've probably said: _Jackpot_.

With almost childlike curiosity, Jack leaned forward towards the screen to get a closer look at the videos presented in front of him. It wasn't nearly as many as the ones he had been overwhelmed by on the front page, maybe only twelve or fifteen, and going by the thumbnails and titles alone, the content they contained was far from similar to the one he previously watched.

Most of the thumbnails were dark or black and white, teasing in nature. Only showing a glimpse of what the actual video contained. A hand over a clothed ass. Dark hair hovering over someone's naked crotch, hiding the face of the person in the video. Long, slim legs on a bed, a skirt half way up revealing white panties. And a black and white frame of a hand around a man's penis. All of them with a glowing little yellow star next to the video title.

Jack swallowed and pressed his palm against his crotch. The last one had looked promising.

' _CUTE TWINK GIVES STRAIGHT MAN THE HANDJOB OF HIS LIFE_ ' 🌟

He frowned at the title, but clicked on the thumbnail nonetheless. It didn't matter that he didn't exactly understand what a _twink_ was, and it turned out, as soon as the clip began, it didn't matter at all.

It was filmed at an awkward angle, in a badly lit room, with the camera shaking slightly at first before the image stabilized from an upwards angle to the side. There was a man on a bed, well, the lower part of a man. He was sitting on the edge of the mattress, wearing jeans and no shirt, and the frame cut off right over his chest. His jeans were tight over his crotch, the top button undone, and a small tent right under the zipper, pushing against the fabric of the jeans.

The man pressed a palm against himself and let out a grunt. His hand was big and his arm looked strong, like he was the kind of man who worked a physical job and knew how to use his weight and his hands.

Kind of like Dean.

Jack shuddered and mimicked the motion, pressing his own palm against his crotch. It was nice like this, watching the man on the screen as he palmed himself lazily through his pants. The fact that he was completely anonymous made it even better, it meant Jack could pretend what he looked like. It wasn't hard, not with the memory of Dean so vivid in his mind.

Unlike the last video that he watched, this one didn't cut between scenes. The camera was static and it kept rolling, building tension deep inside of Jack's chest as he watched the scene unfold on the screen. After a minute or so, the guy stood to pull his jeans off, and there was a loud noise as if something brushed against a microphone. Then another set of legs walked in front of the camera.

The new person was much smaller than the man was, slim frame but not skinny by any means. He sank to his knees on the floor between the man's legs, his face coming into view. He looked young, perhaps early twenties, Jack wasn't sure. His features were soft, sweet, unruly hair that covered his forehead, something vulnerable in the way his eyes glanced upwards at the man, a hesitant hand on his thigh.

_'May I?'_

The man on the bed didn't answer, but Jack assumed he must have nodded because the other man began to rub his hands along his thighs, closer and closer to his groin until he was palming over the thick outline of his dick, pressing against the boxers. A moment later he curled his hands under the waistline and tugged them off, and the fat head of the man's cock sprung free and slapped against his belly with a small noise.

Jack did the same, eyes transfixed on the screen as he slid his own underwear off. He didn't dare to glance down, not now, not when he was watching. He worried it might ruin the mood and instead used the video as an instruction manual, following their every move.

The boy curled a hand around the man's dick, stroking him with long, languid moves, and Jack followed, hissing at the sensation of his hand around his dick.

_"Now you make a circle with your hand, like this, kind of like a fist but not as tight… And you slide your dick through your hand. Find what you like, try adding pressure, going faster or slower..."_

The words echoed in Jack's mind as he remembered Dean's words, and he tightened his hand around himself. His heart leapt inside his chest when the boy twisted his hand up over the swollen head of the cock, and he could visibly see the man's chest shudder at the touch.

Jack sped up his hand on himself as the video progressed, matching the motion when the boy in the clip rubbed his thumb over the slit. That was when he tore his eyes away from the video for the first time, to look at himself, curious to watch as the small bead of translucent white collected near the pink, slitlike opening of his cock caught on the pad of his thumb. He spread it out over himself, the head of his cock red and glistening and so, so sensitive.

"Aahh…" Jack let out a small breath as he moved the precome down over the head, eyes wide at the sight.

' _Fuck. Do you like this? Do you like my hand?_ '

The voices from the video brought his eyes back up to the screen where the boy was moving his hand quickly up and down the man's cock. Jack couldn't help but wonder what it would be like to do that to someone, if he would get as much pleasure out of it as it looked like the pair in the video did. The man was leaning back on his arms now, chest heaving up and down as the boy fisted his cock expertly.

' _Mm. So hard for me. Looks so good._ '

"So good," Jack mumbled, his lips falling open as something began to tighten in his chest. He could feel his feet tense where they were placed flat against the floor, as if he was leveraging himself as he worked his wrist up and down his shaft.

' _Wanna taste. You ever had your cock sucked by a boy before, hm?_ '

The guy between the legs in the video stopped for a moment, his hand returning to long, deliberate strokes as the guy almost convulsed on the bed, grunting and panting hard. The boy grinned, then he licked his lips and leaned his head down to the man's penis. Jack watched as he pressed the length against his cheek as he kept stroking, placing what looked like kisses near the base of it while the man kept moaning. The boy kissed his way along the length all the way to the tip of it. When his hand reached the top, he rolled the head of the cock into his mouth, sucking on it like a lollipop.

' _Mhmmm..._ '

Jack watched, fascinated. He tried to match the slow speed but his heart felt like it was beating twice as fast as normal in his chest, and he couldn't do what the boy did with his mouth to himself, but it looked good, considering the way the man spread his legs to allow better access to his cock, and then fisted a hand in the boy's hair.

The boy moved for a second to lick over his palm, and this, this Jack could do. He licked the palm of his hand, tasting sweat and salt, getting himself real wet before he wrapped his hand around himself again like the boy in the video did to the man. The boy's wrist worked quickly now, the man's breathing sounded strained, hard, as the boy jerked him off quickly, the head of his cock resting against his lips, and he tongued at it and moaned.

Jack hadn't seen many videos, only two, counting this one, but this was the hottest one so far. The man was moaning now, loudly, his hips buckling upward to meet the motions of the boy's hand, his voice gruff, needy.

' _C'mon, yeah, fuck, just like that_.'

It was too easy to imagine that the man in the video was Dean. The only thing that was missing, really, was his tattoo. At that, Jack closed his eyes and rolled his bottom lip in between as he focused, letting the sounds from the video playing be the only thing guiding him as he worked his hand furiously over his own cock. He could feel something building deep in his stomach, letting out little whimpers as he bucked his hips into his fist.

"Ah, ah, please," he moaned. "Dean."

' _Getting close. Fuck, baby, mmm._ '

Jack groaned. He wouldn't mind doing that to Dean, he thought, not one bit. He wanted to know if his dick looked anything like what he saw in the video, if he'd make the same sounds, if he'd let Jack taste his cock. God, he wanted to taste Dean's cock. He'd work him with his hand first like the boy in the video had, he'd tell him sweet things and rub over him until he was shaking and then, then–

' _Fuuuck..._ '

Jack opened his eyes just in time to see the man in the video steering the boy's head down all the way over his cock, thighs clenching, the boy gurgling and moaning, his hand holding onto the base of the cock for dear life.

"Ah-ah- ahhh," Jack whimpered as his own cock tensed up and he came, thick stripes of white spurting out and over his fingers.

He gasped and panted, adrenaline washing over him until he was vibrating, hand absentmindedly tugging the last of the come out of his cock as he slowly came to, watching as the boy in the video pulled himself off of the man with a grin, wiping at his mouth before planting a kiss to the inside of his thigh.

' _Thank you._ ' The boy said and then he stood up and the video ended.

"Thank _you_ ," Jack said, somewhat bewildered, eyes wide as he looked between the black screen and his sticky hand, heart fluttering in his chest like a butterfly.

That was… that was awesome.


End file.
